


A Winchester-style plan

by Naluforever



Category: Supernatural
Genre: Angel Caroline, Angel Castiel (Supernatural), Angels, Angst with a Happy Ending, Beach Vacation, Bisexual Dean Winchester, Break Up, Caroline is so in love for Sam Winchester, Castiel and Dean Winchester and Sam Winchester are Jack Kline's Parents, Established Castiel/Dean Winchester, F/M, Jack is so cuuuuuttte, Love Confessions, M/M, No Sam/Eileen, Protective Dean Winchester, Protective Sam Winchester, Sam/Eileen break up, The Empty (Supernatural), Vacation
Language: English
Status: In-Progress
Published: 2021-02-15
Updated: 2021-02-15
Packaged: 2021-03-15 23:20:56
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,921
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29444001
Author URL: https://archiveofourown.org/users/Naluforever/pseuds/Naluforever
Summary: After 3 weeks where Sam and Caroline both avoid each other, Dean decides with the help of his beloved angel and their son to make them confess their feelings for each other by taking Jack to the beach.
Relationships: Castiel/Dean Winchester, Sam Winchester/Original Female Character(s), Sam/Caroline





	A Winchester-style plan

**Author's Note:**

> Sorry for any mistakes you may find, I am unfortunately not English.I'm French. However, I try to keep it clear and fairly well constructed.

"Dean, are you sure this is going to work?" the ex-angel of the Lord asked her boyfriend, who was a little overexcited about their plan.  
"Of course, honey, Sam and Caroline have been avoiding each other for 3 weeks. Sam has finally come to terms with his break-up with Eileen while Caroline just refuses to admit her feelings like a certain person who was convinced he couldn't have me," says Dean looking at him lovely. 

Castiel rolled his eyes and summarized their, uncorrected, "Super Plan à la Winchester written and validated by Dean", a plan that was far too long if you wanted his opinion. Dean would go and talk to Caroline and Cas to Sam, claiming that Jack needed to go to the beach but that they, the loving parents of their beloved son who were also part of the plot, couldn't, because they had had an "impediment".

"Are you sure we're not going to make things worse between them?  
"Of course not and then those two idiots helped us get together so we definitely owe them a helping hand. Although I feel sorry for the kid for wanting to be in the middle of all this sentimental crap."

Dean took Castiel's chin and bent it to place a tender kiss on his lips.

"Let's get started, and when we're done we'll meet in my room for a briefing and maybe some more."

Castiel blushed and Dean kissed him one last time with a shit-eating grin on his face as he set off to find his target. He had chosen the first angel of creation on purpose, because although she was able to see human emotions and feelings, putting two angels in the same room had turned out to be quite an enriching experience, you could build an iceberg given the calm between them. Not that Caroline hates talking with Cas or vice versa, but rather that neither of them will do the talking preferring the calm, tea and little smiles of friends as if they were talking to each other.  
He found it exactly where he wanted it, a storage room with some old offices that she was renovating so that they could use it later. She was standing with a book in a foreign language, perhaps Latin, Dean thought to himself, in one hand and in the other her phone was sticking to her ear. Dean remained silent at the door waiting for her to notice it, she put the open book on the desk in front of her and turned her back, she didn't seem to notice him. Dean could tell that the person she was talking to was making her quite uncomfortable. 

"Look Jody, it's complicated right now, but I can get the message to Dean to pass it on."

A pause and then she froze completely, which made Dean smile, because Jody was a little piece of woman who could make angels very human.

"No we didn't fight, I promise you... Yes you can call Dean to make sure." She finally turns around but frowns when she sees Dean at the door smiling.

"Speaking of the wolf... Uh no, it's Dean. Ok I'll tell him, don't worry Jody, say hi to the others for me. Yeah, I'll try and talk to Sam, but I assure you..."

Jody had probably hung up because of the way she was looking at her phone, Dean made a mental note to invite Jody and the girls to thank them for their help which was not part of his plan. Caroline sighed and leaned against one of the desks to look at Dean, she pursed her lips and raised an eyebrow.

"Jody says hello. Dean you're up to something, aren't you? I see some mischief and I might not be sure I want to know in case I don't like it."

"Okay Riley, tell Joy, Sadness, Fear, Disgust and Anger to make room for a newcomer."

"Dean you're being sarcastic, Vice Versa is the most unrealistic children's cartoon about human feelings..."

Dean raised his hand to stop her rambling, she was not in a good mood which was still new to him, as she was usually as cheerful as a sunflower in summer and her references would be better received. The only difference between this angel and his was that she understood these references whereas Cas was more the type to bend her head to the side in a lovely way. He got lost in his thoughts when he finished Caroline always looked at him a little more calmly.

"Where's Castiel?"

"He went to see Jack, to explain the situation."

"What situation?"

The plan was finally about to begin

"Cas and I promised Jack we'd take him to the beach, except some hunters called me to help with Cas, so I told them to come by the bunker so we could talk about their case."

Lying was his greatest talent, but doing it in front of a human emotion detector right in front of him was very tempting.

"I can take him there if you want, I know he's already told me about it so I can do it for him".

She returned to her usual smile and her brown eyes regained their calm tone.

"I don't want to disturb you, if you have things to do...

"Don't worry about telling me exactly when and if I have anything that day then I'll cancel to make Jack happy."

" We told Jack on Saturday and we planned to stay in a bungalow in Siesta Beach, Florida for 3/4 days."

She thought it over and gave him her best smile after her time of reflection.

"I'm free on Saturday, nothing planned for 3/4 days at the beach and tomorrow I can take Jack shopping".

"Cas and I owe you a favour, we're trying to finish up as soon as possible to get to you both."

He approaches her and gives her a brief friendly pat on the shoulder, she smiles at him, but the gleam in his eyes disappears as if his subconscious has gone elsewhere. Since his return to the bunker, after they have finally finished with Chuck, this kind of moment happens often, too often as if someone or something is drawing him to a dark place. He shakes her, she comes back to her a little surprised, she touches his shoulder to calm him down.

"You can tell me, you don't have to hide it, we're all here to help you."

"I know, Dean it's just that..." She stops to find the right words and then frowns, because they don't seem to come and she resigns herself to finding them.

"I'm worried about Sam, it's nothing really serious, just... Maybe I had a fight with him about something and we've been avoiding each other for three weeks.

"Sammy is an idiot who thinks that eating rabbit food is normal! So, whatever you've been thinking should be okay in a little while. "

She looked at him amused and then she couldn't hold her laughter back for long, which resounded like the song of a canary throughout the room, she calmed down.

"What was your argument about?"

Dean didn't want to know but it was to help and not spoil his genius plan, he felt her freeze and he could see her lose her smile for two seconds, she pretended nothing had happened by clearing her throat and smiling at him again.  
"You know trifles, like putting the books in the right places or that I'm going to cook a nice dish without a salad tonight. That sort of thing"

He didn't need his angelic power to understand that she was really lying as badly as Sam was when he was seven years old. Cas arrives at the door of the room and looks at Dean with his famous I NEED TO TALK NOW look, Dean smiles a little and then leaves with Cas to their room.

Once inside, Dean let out a huge sigh that he had held all the way down the hallway to the room.

"She's agreed to take him on Saturday."

"Sam too"

Cas took a seat on their bed and tapped the seat next to him, Dean sat down and looked worriedly at his angel.

"What's going on? Did Sam do something stupid during your conversation? "

The instincts of the older brothers as protectors were awakened, but were soon calmed by Castiel.

"No, he wanted to talk to me about something, so I listened."

"So? Is it serious?"

"Dean, did Caroline have them absent when you talked to her?"

"Yeah, but what does this have to do with Sam?"

"Sam told me that's what their fight was about. He also said some things but made me promise not to say anything. "

"Come on, Cas, spit it out!"

"Sam told me that he found out who brought me back from the Void, you remember it wasn't Jack, Amara or the Empty itself. I told you that I didn't remember who took me out either, but Sam he was 100% sure who it was until he could confirm it"".

"And then who is it? "

"Dean who was the closest person to the power of God when we met him?"

The cogs in Dean's mind started moving, he opened his mouth because he had finally understood.

"You mean it's..."

"Yes, it was Caroline who brought me back from the Empty. She confirmed it to Sam during the argument, according to him ''She did it to make you happy and alive again''. There were some side effects when she brought me back, he doesn't know any more except that from time to time she seems not to be really with us and in a very bad mood".

There was an enormous silence and then the hunter passed his hand over her face.

"This angel is really a stupid to the end, we would have found a solution if she had told us about it".

"Sam's researching as best he can on the Empty, do you think your plan is fucked?

"No, it seems not, but now that I know that thanks to her you're back, I just want to go to Sammy right now and tell him to go marry her or keep her with him forever."

Her angel smiles tenderly at her and takes her hand to hold it in his own.

"We owe him a lot more than you expected."

"We owe her a lot, without her you'd still be stuck there and I'd be a huge alcoholic and depressive wreck".

Someone knocks at the door and doesn't wait for the answer to show his little head to the two men. Jack was all smiles when he jumped between Cas and Dean still sitting on their bed.

"What's up, Kid?"

" Caroline came to tell me she was taking me to the beach and to the shop tomorrow, Sam came to tell me after her without running into her. Your plan is working like a charm, Dean."

Cas looked at Jack with his best fatherly smile while Dean smiled, because his plan is working.

"Of course it's working, remember your part? "

"Yes, I won't say anything until Saturday. They will be surprised to be both waiting for me and once I arrive in front of them I give them a huge hug that they will have to give me back. Then, during the journey, I send messages every hour for a report and if they argue I give them my best behaviour as a sad child".

Dean tousled her hair and gave her a big smile.

"All right, when we get to the beach, I'll send you the rest of the plan." 

\----------------

Saturday came rather quickly, Dean was in the kitchen preparing the sandwiches in the cooler and the drinks. Sam had asked him for the Impala and promised him that he would pay with his life if he arrived unhappily at Baby. It was 9.30 am, the departure would be at 10 am. Caroline arrived in the kitchen with a rather lost look on her face and took the cup of tea that Dean had prepared for her, she thanked him with a small smile. Cas was surely with Sam to put the stuff in the trunk and Jack fulfilling his role as latecomer.

"So happy to go to the beach with Jack for 3/4 days?"

" Of course, Florida beaches are famous for their beautiful oceans and the sky should be on our side for a moment of tanning."

She was dressed in a blue tank top and jean shorts, a pair of sunglasses on her long black hair, she had given up her London schoolgirl look for a day at the beach.

"Great look ''.

"Thank you, Jack chose it for me because he told me that my usual clothes were going to be awkward so I trusted him''.

She looks at her phone lying next to her.

"It's almost time to go, Jack's running a little late, I wonder where he is?"

" That's exactly what I came to see"

Dean watches his brother and behind him Cas is apparently not very comfortable. Dean gives a convincing smile to the people in front of him while Caroline continued to stare at his cup and its contents as if to disappear from the room.

"Dean, I don't know what you are planning to do but what is all this supposed to mean? I thought it was just me and Jack." 

"Sammy, calm down. I offered to do the same to Caroline before I knew Cas had asked you to do it."

Caroline closed her eyes and took deep breaths, which worried Dean and Cas.

"Everything's all right," Dean asked, quite surprised by the scene in front of him.

"Yes, everything's fine, I was just surprised." She squeezed her cup tightly enough and opened her eyes again.

Sam seemed to be quite angry with Dean because when he looked up at his brother he was giving him deathly glances.

"Sam, it's just a trip to the beach with Jack, two adults are better than one."

Castiel was very quiet, but he kept staring at the other angel with concern, because he felt something was coming.

"Yes, a day between two adults who strangely aren't getting along very well right now."

"Sam, you could be less of an asshole and more..."

He didn't have time to finish when a sound of broken glass spread across the room and two cutlery drawers flew across the room without anyone touching them. All eyes turned to one and the same person. Caroline looked at the broken cup in her hand, no wounds just from the glass and empty eyes.  
She turned towards Sam with her purple angel irises, they stared at each other for a long time before she spoke.

"Jack is coming, let's make peace in front of him and you can keep avoiding me and cursing me after we get home."

Sam was about to answer when Jack arrived happily, he pulled the handle on Caroline and Sam to give them a huge hug which they gave awkwardly. They separated and Jack stared curiously at Caroline.

"Why are your eyes always purple?"

Caroline fluttered her eyes and they turned brown again.

"I showed them to Dean for fun and to scare him. Are you ready to have some fun?"

"Yeah, plus with the two of you it should be really cool and fun."

"Jack, remember to be polite and a good boy," Castiel said.

"Don't worry, Cas, Jack will be as good as a picture," said Sam.

Jack gives his parents a hug before leaving for the garage with Caroline and the cooler. Sam stayed to fix the contents of the drawers to the floor.

"Dean already knew about this Sam, what happened just now was different from those moments of absence or mood swings," says Cas

"Yes, it's usually either one or the other, but not both at the same time and drawers flying across a room like a fucking Paranormal Activities" says Dean

"It's both your fault we're in this situation, if you'd told us we were going to be together for the trip we could have prepared ourselves mentally for all this".

"Sam will keep an eye on her during your stay, if anything bigger happens you give us a quick call and we'll break in with "Air Angels"".

Sam sighed a huge sigh and looked at his brother a little more calmly.

"Yeah I'll keep an eye on her. After what's just happened she'll probably hide her other symptoms so we don't have to worry."

Dean moved closer to his little brother and gave him a huge pat on the back.

"Going to the beach is waiting for the three of you. Cas and I will finish our work as soon as possible and join you in this corner of paradise".

"Jerk"

"Bitch, get out of here before I change my mind about my car."

\-----------

After the vacationers had left for Florida, Castiel felt Dean sneak up behind him for a hug.

"What are we gonna do until we get there?"

"Good question, Cas, what are we both gonna do here?"

"Clean up the mess in the kitchen?"

"I have a better idea which is to..."

He whispered the rest of his sentence in her ear, making Castiel blush.

"Dean Winchester, you're really lucky I love you. "

"I'm the happiest asshole in the universe."

**Author's Note:**

> I am thinking of making three parties but maybe two will be enough. For the moment the second part seems rather blurry in my head so I hope that after a good night's sleep I will have something to go on again.   
> Hopefully this will be clear enough.


End file.
